Production of organic solvents.



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PR-UD'UCTION F URGANIC SOLVENTS.

T,ll4l,25& Specification of Letters Patent.

Ito Drawing.

a To all whom it may concern: 1

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tit

Be it 'knownthat I, FIN SPARRE, of Wilmington, in the county of New Castle, and in the State of Delaware, have invented a certain new and useful Improvement in the Production of Organic Solvents, and do hereby declare that the following is a full,

clear, and exact description thereof. V

My invention relates particularly ,to a

process of producing solvents from the parafiin hydrocarbons and derivatives thereof and especially the halogen derivatives thereof, although it is applicable also to the production of solvents from other compounds.

My invention also relates to a novel mix ture of solvents which. is obtained by the process referred to, r

The object of my invention is to providea process for obtaining solvents'having great utility, at a minimum cost andwith the expenditure of-a minimum amount of labor.

A further object of my invention is to produce a solvent mixture having valuable ,properties for use as a solvent in many different industries, but which will be particularly adapted for use in producing nitrocellulose coatings.

Stillaiu her object of my invention is to produce a productof this kind with a small number of chemical operations, my invention being designed to dispense with the step of distillation for separating the' as embodiments out my invention, as one follows: One of the hydrocarbon fractions,

preferred form thereof I may "proceed as hnown'in the trade as gasolene,'naphtha, or benzin, may be used-as a starting point. Assuming thatthe process is carried-out with gasolene, the same is distilled so as to obtainthefraction boiling between 28 C. and" 69 C. The fraction thus obtained will consist of p entane, isopentane, hexane and isoheXaneshis product, which I will refer to as the pentanes and hexanes, is chlorinated by treatment with -chlorin in the presence of light, until the proper degree of chlorina- -While many examples might be supplied character.

Application filed October 19, 1912. Serial No. 728,609.

tion is efiected. This chlorinated product Wlll contain, among other constituents,

monoand di-' chlor substitution products of the pentanes and hexanes, and perhaps some of the higher chlorhydrocarbons. It might seem desirable at this point to separate the chlorhydrocarbons by distillation, but I find it desirable and advantageous to entirely dispense with the step of distillation to separate the chlor-hydrocarbons at this point 1n the process. It is advantageous to dispense with the stepof distillation to separate chlorhydrocarbons at'this point as such distillation results in breaking down some of the chlorhydrocarbons. carbons thus obtained, and without previous separation, are then subjected to the step of acetyla'tion by treatment with sodium acetate and acetic acid in the usual manner. As a result, the liquids treated become changed over into olefins, chlorolefins, mo-

The chlorhydronoacetates and diacetates' yforj example, a

chlorhexylenes, amyl and hexyl acetates and amylene and hexylene diacetates obtained from a treatment of chlor entanes and chlor hexanes-and there is ormed during the acetic acid, as well as a small percentage of tarry impurities. The solvent mixture is a then separated from the sodium chlorid and acetic acid. The solvent mixture thus obtained comprises constituents which boil from approximately C. to approximately. 250 (3., and theproportions of the several constituents will be found in some instances to be approximately as follows: olefins, chlorolefins, 5%, monoacetates, and diacetates, 10%.

The diacetates'are excellent solvents, especially for nitrocellulose compounds, and the monoacetates are very good solvents, but

'amylenes, hexylenes, chloramylenes, and

treatment a quantity of sodium" chlorid,

have not quite ,the'solvent power of thediacetates. The chlorolefins are poor' sol vents, while the olefins arenon-solvent in The monoand diacetates are such good solvents, however, that the olefins and chlorolefins may act as diluents thereof without causing thedis'solved materials to separate out. The percentages of these several constituents are such, furthermore, as not to cause the dissolved materials to separate out. and, intact, the presence of the nonsolvents and poor solvents with the good solvents increases the total amount of marot are

rial which may be dissolved in the quantity of good solvents present. In this solvent 7 mixture the olefins have boiling points ap- .ing 65% of the proximately between C. and 75 (3., while the remaining constituents of the mixturefare above approximately 75 C. Approximately 35% of this mixture is made up of those monoacetates. present which are high boiling and the diacetates present, all of which are high boiling, while the remainmixture is made up of the remaining low boiling monoacetates, the chlorolefins and the olefins, the two last mentioned classes of compounds present being all low boiling. This is particularly valuable in a solvent or solvent mixture used for nitrocellulose compounds and similar compounds, as it is desirable to have the greatest percentage of the mixture of such a nature that it will evaporate quickly and therefore permit the compound to dry rapidly, but it is also exceedingly desirable After fractionation,

' approximate the desired to have a small percentage of the solvent evaporate slowlyfas thereby a tougher product is obtained. Should it be found desirable, however, the solvent mixture thus obtained in any other desired, manner, and the several constituents thereof may be applied to any use which may be found desirable. the various constituents obtained may be used separately as solvents, or they may be mixed so that at least one low boiling constituent is mixed with at least one high boiling constituent, so as to properties of the solvent mixture desired.

While I have described my invention above in detail, I wish it to be understood that maniy changes may be made therein wiiholut eparting from the spirit thereof.

1. The process which comprises acetylathexane and ing a chlorinated may be separated by fractionation or ing a halogenated mixture of pentane, hexane and their isomers, and separating out the solvent bodies thus produced.

2. The process which comprises acetylating a halogenated mixture of pentane, their isomers, separating out the solvent bodies thus produced and frac- -tionating the solvent bodies thus obtained.

3. The process which comprises acetylatmixture of pentane, hexane and their isomers and separating out the solvent bodies thus produced.

4.. The process which comprises acetylating a chlorinated mixture of pentane,

hexane and their isomers, separatmg out the solvent. bodies thus produced and fractionatingthe solvent bodies thus obtained. 5. The process which comprises a'cetylating pentane, hexane and their isomers.

6. The process which comprises acetylating a mixture of chlorin derivatives of pentane, hexane and their isomers.

7. A solvent mixture comprising a chloramylene and a monoacetate.

8. A solvent mixture comprising an olefin, adralogen derivative of'an olefin, a monoacetate and a diacetate..

9. A solvent mixture comprising a halogen derivative of an olefin, a monoacetate and a diacetate.

- 10. A solvent mixture comprising an olefin, a. chlorolefin, a monoacetate and a diacetate.

11. A solvent mixture comprising a chlor olefin, a monoacetate and a diacetate.

In testimony that I claim the foregoing I ha e hereunto set my hand.

FINSPARRE.

Witnesses:

W. G. TOTNAIL, Jr.,

A. M. GORMAN.

a mixture of halogen derivatives of 

